


Always be on time

by Silvaxus



Series: SPN Heaven & Hell Bingo 2019 [7]
Category: Supernatural
Genre: Alternate Universe - Human, Anal Sex, BDSM Scene, Bad Dragon Toy, Blindfolds, Bottom Dean Winchester, Bottom Rowena MacLead, Cock Cages, Domme Rowena MacLeod, Erotic Electrostimulation, F/M, Impact Play, Paddling, Pegging, Spanking, Sub Dean Winchester, Top Dean Winchester, Top Rowena MacLeod, Topping from the Bottom
Language: English
Status: Completed
Published: 2019-08-09
Updated: 2019-08-09
Packaged: 2020-08-13 15:09:21
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,578
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20176318
Author URL: https://archiveofourown.org/users/Silvaxus/pseuds/Silvaxus
Summary: At the beginning, something had been made very clear; be on time, always. being late would force the beautiful redhead to punish him.Dean was late and he could already feel his mistress’s firm hand connecting with his skin.





	Always be on time

**Author's Note:**

> Song Challenge Bingo Square: Addicted to love  
Crow's Bingo Bingo Square: Clubbing  
Heaven & Hell Bingo Square: All Human AU
> 
> Credits for the edits for my beloved Beta [CrowNoYami](https://archiveofourown.org/users/CrowNoYami/pseuds/CrowNoYami)

When Dean killed the engine of his car in the parking lot of the club, he knew he was in big trouble. He was late, and his mistress hated nothing more than Dean being late. He was sure his punishment would be severe. He would be lucky if she would allow him even one orgasm.  
  
Exhaling until his lungs protested, Dean left the car and walked to the entrance of the club. On the outside, it looked like any nightclub, but on the inside, it was one of the classiest BDSM clubs in the state.  
  
Dean flashed his membership card at the burly bouncer who let him in without any trouble. With a glance at the barkeeper while passing, who nodded, Dean was on his way to their standard room.  
  
Using the stairs to the basement, Dean stopped when he reached his destination. Suddenly he was more than just nervous. He fixed some non-existing wrinkles on his shirt before he knocked on the door.  
  
There was no sound, but suddenly the door opened, and a stunning redhead in a silky robe colored in black and darkest violet stood in the doorway. The sensual smirk on her face made Dean shiver.  
  
“Well, well, well. What do we have here? We are a wee late, aren’t we, Darling?”  
  
Nodding, Dean lowered his eyes and stared at his Mistress’s perfectly done toenails.  
  
“Yes, Mistress. I apologize for being late.”  
  
When Rowena stepped aside and held the door open for him, Dean walked into the room, the door closed behind him.  
  


Dean held his position in the middle of the room without looking up. Rowena was sauntering around him, silent and dangerous as a jungle cat. Her small hand wandered teasingly over Dean’s body.  
  
“You remember how much I hate it when you are, Dean. Yet here you are late once again.”  
  
Feeling her disappointment was almost worse than her looking at him when he failed to follow her orders.  
  
“I’m sorry, Mistress. I didn’t mean to be late.”  
  
Rowena made a clicking sound with her tongue, and delicate fingers made Dean look up.  
  
“I know you’re sorry because you know I will punish you now. While you were on your way here, I took my time to think about your punishment. Time to strip my pretty Darling.”  
  
Nodding, Dean started to remove his clothing and put them away, neatly folded. Rowena, meanwhile, had her back turned to him and was preparing whatever she had in mind.  
  
Once he was completely naked, Dean stood there with his back held straight and looking straight ahead. When Rowena stood once more in front of him, she held a long silken strip of cloth up to him, a blindfold.  
  
“Help yourself to the first part of your punishment. You have to work to get this off.”  
  
Taking the blindfold from her hands, Dean wrapped it tightly around his head and over his eyes. Probing fingers tested the tightness of the blindfold before those same fingers tapped against his thighs.  
  
“Spread your legs and stay where you are.”  
  
Shifting in his stance, Dean held his position even when he felt nimble fingers playing with his free-hanging balls and cock.  
  
The weight of the tight cockcage was something Dean expected, just like the weighty and fitted metal ring around his balls. Grunting as Rowena tugged once more on his balls, Dean’s mistress wrapped her fingers around his wrist.  
  
Even in his blindfolded state, it was easy to trust Rowena to led him through the room. Dean’s trust in his mistress was absolute. He didn’t hesitate to go lax in her steady grip like it was natural for him to accept the next part.  
  
His mistress was humming to himself while she instructed Dean to lay down what felt like a breeding bench. They didn’t use it often, and Dean knew that whenever Rowena made him bend over it, he would feel his mistress for the days to come.  
  
Dean found himself strapped down on the bench. His arms and legs were strapped down with cuffs attached to the legs of the seat. The bench design allowed Dean to rest comfortably on the soft padding while his head was supported like he was waiting to get a massage. The unique design of the bench allowed his junk, currently bound tightly in the cage and the ball ring, to hang freely to allow his mistress access to his vulnerable parts whenever she desired.  
  
Dean took a deep breath and allowed his muscles to relax while he heard his mistress walk around while making clicking sounds with her tongue; a sign that she was considering the next part of Dean’s punishment.  
  
“You were 36 minutes late, my pretty darling. This means quite the spanking for your soon to be red behind.”  
  
Dean swallowed. His mistress had a heavy hand if she was in the right mood and Rowena was in the right mood for a severe punishment.  
  
“Twelve hits each will be sufficient. Twelve with the paddle, twelve with the riding crop and twelve with your favorite; my hand.”  
  
Dean shivered at the promise of pain but didn’t answer otherwise. His mistress hadn’t told him to speak after all, and he could already hear his mistress prowling around him like a jungle cat while he dragged the heavy paddle over his bare back.  
  
“Your safeword, my darling?”  
  
The warm wood pressed against Dean’s naked ass and he tried not to wiggle when Rowena pushed against the plug he had been wearing since he walked out of his home.  
  
“Cherry Pie,” was Dean’s prompt answer which turned into a soft gasp as she pulled the plug out.  
  
“As much as I appreciate your eagerness, because I will make good use of your hungry hole later, for now, we won’t need this while you get your punishment.”  
  
The first hit with the paddle followed Rowena’s words like the snap of a whip. Even with Dean expecting it, it hurt before a warm tingle started to spread. There was no need for Dean to count the hits, he wasn’t told to do so, and because he knew that Rowena would go with the punishment as promised.  
  
Her smacks always came with the same tiny break in-between before the next one followed. If Dean could move in his current position, he would rub himself all over the soft material of the bench. Rowena’s hits were hard, and she spread the slaps all over his ass and parts of his thighs, but every strike was a numb and warm pain.  
  
The sensation changed when she was finished with the paddle after the promised twelve hits and exchanged the paddle for the riding crop. It was Dean’s least favorite toy. The pain was sharper, the sting almost biting in his flesh, and while he didn’t fear that Rowena would break his skin with the crop, it always felt like a close call. The last strike of the crop was the one that made Dean yell in surprise, and he could feel the wetness leaking from his caged cock.  
  
The tip of the riding crop hit his exposed hole with a sharp snap, and it was so startling that Dean was grateful for the cage around his cock. The intense and sudden pain always turned him into a panting mess, and Rowena knew that as she dragged her fingers through his hair like a caress while she put the riding crop aside.  
  
The next twelve hits, delivered by Rowena’s bare hands, were over fast and with a mix of pain and pleasure Dean carved every time Rowena allowed him to feel her hand hit his flesh. He craved the feeling more when it was over.  
  
“As always, you took your punishment like a good boy. You get to relax for a moment while I prepare the next part.”  
  
Dean heard the dark promise in her words and when he heard the sound of leather and metal scraping against metal. He couldn’t hold onto the wanton moan leaving his mouth.  
  
“So hungry to be filled, aren’t you, my sweet boy? I bought you a gift for today, and as much as I think you are far from having earned a gift today, it will be so much fun to see you come apart by my it.”  
  
Something pushed into Dean’s hand, and Rowena moved it around in his palm so he could feel the size and texture. It was huge with ridges and bumps all over the surface, and he had trouble to form a picture in his mind before his traitorous mind offered him the right image.  
  
Whining, Dean ducked his head to hide the flush he could feel crawling up his face. He knew precisely what Rowena had purchased for him. It was something from a homepage Dean had showed her, and she must have seen his excitement at one of the toys. It was big, had an enormous girth and was called Hunter, a monster of a dildo the way it felt between Dean’s fingers moments ago.  
  
“Ah, I see you know my gift, boy. Since you were a good boy for me before you were late, I will make good use of your foresight and will enjoy myself since you are still indisposed.”  
  
Dean went limp in his strapped down position. He loved it when Rowena fucked him hard and the bigger the toy, the better. Usually he came after he few thrusts and Rowena would fuck him without mercy until he ran dry but today…  
  
The snick of a bottle of lube opening pulled Dean out of his mind. Moments later, he felt the push of the toy’s broad head against his hole. In no time the toy’s enormous girth stretched Dean’s rim to the point of pain, but Rowena would pull out whenever Dean’s back tensed.  
  
His mistress took her time to work Dean open with nothing but the thrusts of the toy strapped to her harness around her slender hips. Her thrusts were slow and deep with a cruel aim behind her movement that rammed the big and unyielding toy every few thrusts into Dean’s prostate the more of the toy worked into Dean’s tight channel.  
  
Only when Dean felt his mistress smooth skin against his spanked red and hot ass did he realize that she had worked the toy all the way in. Moaning against the fullness, Dean could picture the steady stream of precum leaking down from his cock. Rowena’s sharp nails dug into the skin of his hips before she started to thrust and Dean knew from their past that Rowena’s strap-on harness would offer her pleasure as well as she was fucking him.  
  
Her needy and breathless gasps were like music while she fucked Dean hard and fast and arousing carelessly. He had disappointed his mistress, and now she was using him for her pleasure while his was a minor matter.  
  
Behind Dean, Rowena moaned and gasped loudly, captured in her pleasure while Dean mewled and whined while she worked his prostate over and over with fast thrusts and the hardness of the toy offered no mercy. His whole body started to jerk when Dean was pushed over the cliff and into an orgasm that was part relief and part madness as it offered almost no feeling of a release from his pleasure. Rowena didn’t stop her thrusts as she was chasing her orgasm.  
  
Only when her sharp nails dug in hard, and she tensed behind Dean did he know that his mistress had reached her release. When she finally pulled out, Dean felt completely open and empty, and he whined at the feeling.  
  
The sound earned him an amused chuckle from his mistress, a pat to his still red and sore ass before he felt a new toy pushed into his hungry hole.  
  
“Don’t worry, Darling. I know how much you love being filled. Relax a moment before I free you.”  
  
Dean clenched around the toy in his ass while he listened to his mistress getting out of the harness. He enjoyed her gift.  
  
Warm and tender fingers opened the cuffs around his arms and legs, but he wasn’t allowed to get up before she took the blindfold off as well.  
  
Blinking against the light, Dean rubbed his eyes and accepted his mistress’ help to get up. She led him over to a comfortable chair that would allow her to ride him in a comfortable position. He was told to sit down, and he found his legs strapped down once more with the cuffs hidden behind the backrest of the chair. A spreader bar was fixed between his ankles, and Dean was surprised when Rowena freed him from the cock cage and the ball ring.  
  
Looking up at his mistress, Dean felt himself getting hard slowly only to grow fully erect as she showed him the small remote in her hand. When he gave a clipped nod, did she push the button and the toy firmly embedded in Dean’s ass came to life.  
  
It was something they had discovered by trying new things Dean had a kink for electro stimulation, and Rowena was sadistic enough to make him lose his mind with the help of his kink. Dean cursed at the first spark of electricity racing through his body. Through his still abused prostate, followed immediately by the next jolt.  
  
He was too captured in the pleasure provided by the toy, or he would have noticed Rowena sitting down in his lap earlier. Nimble fingers wrapping around his cock made Dean pull on his restrains. He wanted to touch his mistress, bury his fingers in her long and dark red hair while he kissed the slender column of her throat. However, he was trapped in his position and had to watch his mistress fuck herself down on his cock. Her small breasts were out of reach for Dean to suck on the rosy nipples and the double stimulation, from her wet and tight walls and the electro stimulation from the toy, made Dean cum into his mistress embarrassingly fast.  
  
Rowena helped him to ride out his orgasm to the last drop before she switched off the toy. She allowed him to go soft in her, and he could feel the sticky slickness of his release start to cover his skin before she rose.  
  
She freed him from the spreader bar and released his arms only to massage his limbs to get the blood back to flow. She offered him a water bottle while she was working on his numb limbs, and Dean enjoyed the strength behind each grip of slender fingers.  
  
She allowed him a moment to rest before holding his collar with a smirk on her face, and Dean didn’t know if he was suddenly feeling warm or cold. The collar always meant one thing.  
  
“While you were late I booked us an appointment for the main stage. Sam, Castiel, and Lucifer were all too eager to join us. We should get going; we are scheduled to be on stage in 5 minutes.”  
  
Dean lifted his head and allowed her to snap the collar around his throat. The leash was held tight in her hand, and he followed her obediently. Music was blasting loudly, and Dean could hear it clearly while he was led to stage.   
  
_There's no doubt, you're in deep_

_Your throat is tight; you can't breathe_

_Another kiss is all you need_

**Author's Note:**

> And here you can find said bad dragon toy:  
[Hunter](https://bad-dragon.com/products/hunter)
> 
> For more of my insanity, find me on tumblr: [Silvaxus](https://silvaxus.tumblr.com/) You want on my taglist on tumblr? No Problem! Write me a message either here on Ao3 with your tumblr tag or write me on tumblr.


End file.
